I've been using Python professionally since 2000 and have never run into issues with its tooling. It's even easier these days: "python -m venv" and then pip are all I need in 99% of use cases. For local development I use direnv + pyenv. I typically develop on macOS and deploy to either macOS or Linux. I previously gave pipenv a try but found it to be brittle and more trouble than it was worth. I haven't used poetry just because I haven't had the need.
Conversely, I regularly run into trouble with ruby. Here's a recent example where I had to contribute a patch to pre-commit to get ruby to install gems where pre-commit wanted it to:
https://github.com/pre-commit/pre-commit/pull/2905
I got so annoyed with bundler I wrote a simple shell script to provide the moral equivalent of Python venvs to gem:
https://gist.github.com/jaysoffian/3c67711d3f00c364365905d87...
All that said, these are just minor annoyances. The only tooling I truly despise is Gradle and especially everything around the Android Gradle Plugin.